Olivia Rodrigo’s dating stories apparently left Chappell Roan with one very direct suggestion: she should consider dating women instead. The pop stars’ studio conversations took an unexpected turn while they worked together, giving fans a glimpse into the friendship behind their new musical collaboration.
The singers joined forces on a remix of Rodrigo’s song “expectations,” released alongside a music video on October 15. Beyond the music, their candid conversations revealed how Roan’s confidence and attitude helped inspire the track’s message.
Olivia Rodrigo shares why Chappell Roan suggested she should start dating girls
During an interview with Apple Music’s Zane Lowe, Rodrigo, 23, recalled discussing her romantic misadventures while writing the song. Speaking directly to Roan, she remembered sharing the “crazy stuff that boys have done to me” during their studio session.
“You were like, ‘Oh my God, you need to start dating girls. This is crazy.’ It’s wild out here,” Rodrigo recalled, describing Roan’s reaction. The advice came amid a creative partnership that Rodrigo described as a dream come true. She explained that “expectations” began as an attempt to write something more empowering than her usual emotional storytelling. Rather than simply describing her feelings, she wanted a track that could become a personal mantra.
“I wanted to be like, ‘I want to sing this song every night.’ It’s like Kendrick Lamar, ‘Sit down, be humble,’ it gets in your brain,” she explained during the interview. Rodrigo also credited Roan’s distinctive confidence with shaping the song’s attitude. “So when I made the song, honestly, I was really inspired by Chappell and the attitude and swagger that she had,” she said.
Roan, meanwhile, appreciated that the collaboration made room for queer representation. “I don’t know if everyone would be down to have a fully queer verse on their song,” she said, praising Rodrigo’s support for queerness and calling the track’s energy feminist.
The remix marked Roan’s first-ever featured appearance and followed her 2025 release, “The Subway.” Rodrigo’s album, You Seem Pretty Sad for a girl so in love, arrived in June and debuted at No. 1 on the Billboard 200. Whether Rodrigo takes her friend’s dating advice remains to be seen. Still, their collaboration showed how candid conversations, personal experiences, and a little pop-star swagger can inspire music with a message.
